PTP1B inhibitors: Synthesis and evaluation of difluoro-methylenephosphonate bioisosteres on a sulfonamide scaffold

被引：23

作者：

Holmes, Christopher P. ^{[1
]}

Li, Xianfeng ^{[1
]}

Pan, Yijun ^{[1
]}

Xu, Caiding ^{[1
]}

Bhandari, Ashok ^{[1
]}

Moody, Claire M. ^{[1
]}

Miguel, Joy A. ^{[1
]}

Ferla, Steven W. ^{[1
]}

De Francisco, M. Nuria ^{[1
]}

Frederick, Brian T. ^{[1
]}

Zhou, Siqun ^{[1
]}

Macher, Natalie ^{[1
]}

Jang, Larry ^{[1
]}

Irvine, Jennifer D. ^{[1
]}

Grove, J. Russell ^{[1
]}

机构：

[1] Affymax Inc, Palo Alto, CA 94304 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2008年 / 18卷 / 08期

关键词：

PTP1B; phosphatase; bioisostere; sulfonamide;

D O I：

10.1016/j.bmcl.2008.03.007

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

We have synthesized and evaluated a series of triaryl sulfonamide-based PTP1B inhibitors in which a difluoro-methylenephosphonate group of a potent lead has been replaced by potential bioisosteric replacements. Several mono-or di-charged compounds (8a, 8b, and 15a) were shown exhibit inhibitory activity in the low micromolar range, demonstrating the feasibility of using this approach in identifying non-phosphonate pTyr mimetics in a small molecular scaffold. These results also provide a useful indication of the relative effectiveness of these pTyr mimetics. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：2719 / 2724

页数：6

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